Реакция #1483079

Уравнение реакции

4-fluoro-benzyl bromide

1-methyl-1H-indole-5-carboxylic acid methyl ester

4-fluoro-benzyl bromide

dioxane

→

3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

Выход 22.0%

Растворители

ether

Условия реакции

Обработка

1. 1
   Температураwere heated
2. 2
   Температураto reflux for 16 hr
3. 3
   Температураthe solution was heated
4. 4
   Температураat reflux an additional 4 hr
5. 5
   Промывкаwashed with aq. NH4Cl (50 mL)
6. 6
   СушкаThe organic layer was dried over MgSO4
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated

Методика

A solution of 1-methyl-1H-indole-5-carboxylic acid methyl ester (0.17 g, 0.9 mmol), prepared using procedures as described in Example 1, Ag2O) (0.22 g, 0.95 mmol), 4-fluoro-benzyl bromide (0.18 g, 0.95 mmol) and dioxane (4 mL) were heated to reflux for 16 hr, then more 4-fluoro-benzyl bromide (90 mg, 0.5 mmol) was added and the solution was heated at reflux an additional 4 hr. After cooling to room temperature, the reaction mixture was diluted with ether (60 mL), washed with aq. NH4Cl (50 mL) and then brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane, 1:3) to provide 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (58 mg, 22% yield).

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